Bifunctional thiourea-catalyzed asymmetric [3 + 2] annulation reactions of 2-isothiocyanato-1-indanones with barbiturate-based olefins

Jiang-Song Zhai; Da-Ming Du

doi:10.3762/bjoc.18.3

Bifunctional thiourea-catalyzed asymmetric [3 + 2] annulation reactions of 2-isothiocyanato-1-indanones with barbiturate-based olefins

Beilstein J Org Chem. 2022 Jan 4:18:25-36. doi: 10.3762/bjoc.18.3. eCollection 2022.

Authors

Jiang-Song Zhai¹, Da-Ming Du¹

Affiliation

¹ School of Chemistry and Chemical Engineering, Beijing Institute of Technology, No.5 Zhongguancun South Street, Beijing 100081, People's Republic of China.

Abstract

Bifunctional thiourea-catalyzed asymmetric [3 + 2] annulation reactions of 2-isothiocyanato-1-indanones with barbiturate-based olefins have been developed to afford chiral dispiro[indene-pyrrolidine-pyrimidine]s. Through this strategy, the target products could be obtained in good to excellent yields with excellent stereoselectivities. In addition, the synthetic utility was verified through a gram-scale synthesis, one-pot three-component reactions and further transformation experiments of the products.

Keywords: Michael addition; asymmetric catalysis; cyclization reaction; one-pot three-component reaction; spirobarbiturates.